EP0130459B1 - Polyisobutylene succinic acid half esters, their preparation and compositions containing these compounds that can be transferred to an adhesive by means of radiation - Google Patents
Polyisobutylene succinic acid half esters, their preparation and compositions containing these compounds that can be transferred to an adhesive by means of radiation Download PDFInfo
- Publication number
- EP0130459B1 EP0130459B1 EP84106997A EP84106997A EP0130459B1 EP 0130459 B1 EP0130459 B1 EP 0130459B1 EP 84106997 A EP84106997 A EP 84106997A EP 84106997 A EP84106997 A EP 84106997A EP 0130459 B1 EP0130459 B1 EP 0130459B1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/20—Chemical modification of a polymer leading to a crosslinking, either explicitly or inherently
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2810/00—Chemical modification of a polymer
- C08F2810/30—Chemical modification of a polymer leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
Definitions
- the invention relates to new polyisobutylene succinic acid esters of alcohol or acrylic or methacrylic acid esters and to processes for the preparation of these compounds by an esterification reaction known per se.
- the invention further relates to preparations which can be converted into an adhesive by irradiation.
- the invention is based on the object.
- an adhesive in particular a pressure sensitive adhesive
- the usability of such compounds as adhesives presupposes that the radiation-induced polymerization does not lead to embrittlement of the products, but that they still have sufficient flexibility and stickiness.
- the new polyisobutylene succinic acid half-esters therefore still have a free carboxyl group.
- the properties of the compounds according to the invention can be influenced even further.
- the compounds according to the invention are medium to highly viscous liquids. They polymerize when exposed to high-energy radiation, in particular by means of electron beams or UV light, to form sticky masses.
- the compounds according to the invention can be prepared in a manner known per se by reacting polyisobutylene succinic anhydride with equimolar amounts of the alcohol R 2 0H or R 3 0H under esterification conditions known per se and preferably in the presence of a solvent.
- Esterification conditions known per se are understood to mean the conditions known to the person skilled in the art under which esterifications are usually carried out. This includes the use of elevated temperatures, preferably a temperature of 40 to 100 ° C.
- the esterification reaction can advantageously be carried out using a solvent.
- the esterification reaction can in the presence of known catalysts, such as. B. small amounts tertiary amines. In order to avoid undesired polymerization of the acrylate or methacrylate groups, small amounts, e.g. B. 0.02 to 1 wt .-%. Add polymerization inhibitors such as hydroquinone.
- the invention further relates to preparations which form adhesives by radiation, consisting of 30 to 100% by weight of compounds of patent claim 1.0 to 70% by weight of radiation-polymerizable monomers and / or oligomers, 0 to 15% by weight. % Initiators and 0 to 50% by weight of conventional additives, such as adhesive aids, pigments and fillers.
- the preparations according to the invention contain at least 30% by weight of the compounds of claim 1. They can contain up to 70% by weight of radiation-polymerizable monomers and / or oligomers.
- monomers or oligomers are hexanediol diacrylate, 2-ethylhexyl acrylate, trimethylolpropane triacrylate or so-called epoxy acrylates, which are derived, for example, from bisphenol A, urethane acrylates and polyester acrylates, properties of the adhesives, in particular the viscosity and / or the curing rate and / or the adhesive properties.
- the preparations according to the invention can contain up to 15% by weight of initiators.
- initiators can be dispensed with. However, they are required for curing by UV rays.
- Suitable initiators are aromatic ketones, hydroxyketones, benzoin ethers and other compounds known for this purpose, which may also contain activating additives such as amines.
- the preparations according to the invention can contain up to 50% by weight of conventional additives.
- Common additives are e.g. B. agents which are admixed to influence the adhesive properties and are referred to as adhesive agents.
- adhesive agents For example, it is possible to mix in polyisobutylene which is free of functional groups. It is also possible to add pigments and / or fillers as long as they do not impair the adhesive properties.
- solvents is possible, but is generally avoided, since it is an advantage of the compounds according to the invention that, because of their consistency, they can be processed without solvents.
- Typical examples of adhesive aids according to the invention are tackifying products, such as. B. polybutylenes, polybutadienes, polyisoprenes, polychloroprenes, polyacrylates, polyvinyl acetates of various molecular weights, natural rubber, natural resin esters, so-called hydrocarbon resins.
- tackifying products such as. B. polybutylenes, polybutadienes, polyisoprenes, polychloroprenes, polyacrylates, polyvinyl acetates of various molecular weights, natural rubber, natural resin esters, so-called hydrocarbon resins.
- Other suitable products are the expert z. B. from DE-OS 2 340 040 known.
- Suitable fillers are calcium carbonate, silica, carbon black, talc and silicates.
- preparations 1 to 9 penetrate coated papers. These papers can then be easily detached from polyester and aluminum without being destroyed.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
Die Erfindung betrifft neue Polyisobutylenbernsteinsäurehalbester von Alkoholgruppen aufweisenden Acryl- oder Methacrylsäureestern sowie Verfahren zur Herstellung dieser Verbindungen durch eine an sich bekannte Veresterungsreaktion. Die Erfindung betrifft ferner Zubereitungen, die durch Bestrahlung in ein Klebmittel überführt werden können.The invention relates to new polyisobutylene succinic acid esters of alcohol or acrylic or methacrylic acid esters and to processes for the preparation of these compounds by an esterification reaction known per se. The invention further relates to preparations which can be converted into an adhesive by irradiation.
Es ist bekannt, Polyisobutylenbernsteinsäureanhydrid durch Umsetzung von Polyisobutylen mit Maleinsäureanhydrid herzustellen. Diese Säureanhydride wurden als Ausgangsverbindungen zur Herstellung von ungesättigten Polyestern durch Cokondensation mit Glykolen und Maleinsäureanhydrid, von Alkydharzen und von flexiblen Polyolen für die Polyurethanherstellung genutzt.It is known to produce polyisobutylene succinic anhydride by reacting polyisobutylene with maleic anhydride. These acid anhydrides were used as starting compounds for the production of unsaturated polyesters by cocondensation with glycols and maleic anhydride, of alkyd resins and of flexible polyols for the production of polyurethane.
Der Erfindung liegt die Aufgabe zugrunde. Verbindungen aufzufinden, welche durch Bestrahlung die Eigenschaften eines Klebers, insbesondere eines Haftklebers, erhalten. Die Verwendbarkeit solcher Verbindungen als Klebmittel setzt dabei voraus, daß die durch Strahlung induzierte Polymerisation nicht zu einer Versprödung der Produkte führt, sondern diese noch ausreichende Flexibilität und Klebrigkeit aufweisen.The invention is based on the object. To find compounds which receive the properties of an adhesive, in particular a pressure sensitive adhesive, by irradiation. The usability of such compounds as adhesives presupposes that the radiation-induced polymerization does not lead to embrittlement of the products, but that they still have sufficient flexibility and stickiness.
Überraschenderweise wurde gefunden, daß bestimmte Halbester des Polyisobutylenbernsteinsäureanhydrids es gestatten, Zubereitungen herzustellen, die durch Bestrahlung in Klebmittel, insbesondere solche mit Haftklebeigenschaften, überführt werden können und die sich durch hohe Klebkraft, ausgezeichnete Haftklebereigenschaften und Strahlungshärtung unter schonenden Bedingungen auszeichnen.Surprisingly, it was found that certain half-esters of polyisobutylene succinic anhydride make it possible to prepare preparations which can be converted into adhesives, in particular those with pressure-sensitive adhesive properties, by radiation and which are distinguished by high adhesive strength, excellent pressure-sensitive adhesive properties and radiation curing under mild conditions.
Die neuen Verbindungen entsprechen dabei der Formel
- R1 ein Polyisobutylenrest mit einem Molekulargewicht von 100 bis 20 000 ist,
- R2 und
- R3 voneinander verschieden sind und einer der beiden Reste einen Wasserstoffrest und der andere Rest eine der Gruppen
- R4, R5 ein Wasserstoff- oder Methylrest und
- R6 ein Methyl- oder Ethylrest ist,
bedeutet.The new compounds correspond to the formula
- R 1 is a polyisobutylene radical with a molecular weight of 100 to 20,000,
- R 2 and
- R 3 are different from one another and one of the two radicals is a hydrogen radical and the other radical is one of the groups
- R 4 , R 5 is a hydrogen or methyl radical and
- R 6 is a methyl or ethyl radical,
means.
Die neuen Polyisobutylenbernsteinsäurehalbester weisen somit noch eine freie Carboxylgruppe auf. Durch Umsetzung dieser Carboxylgruppe mit Verbindungen, welche geeignete funktionelle Gruppen aufweisen, können die Eigenschaften der erfindungsgemäßen Verbindungen noch weiter beeinflußt werden.The new polyisobutylene succinic acid half-esters therefore still have a free carboxyl group. By reacting this carboxyl group with compounds which have suitable functional groups, the properties of the compounds according to the invention can be influenced even further.
Die erfindungsgemäßen Verbindungen sind je nach Molekulargewicht mittel- bis hochviskose Flüssigkeiten. Sie polymerisieren bei Einwirkung energiereicher Strahlung, insbesondere durch Elektronenstrahlen oder UV-Licht, zu klebrigen Massen.Depending on the molecular weight, the compounds according to the invention are medium to highly viscous liquids. They polymerize when exposed to high-energy radiation, in particular by means of electron beams or UV light, to form sticky masses.
Die erfindungsgemäßen Verbindungen können nach einem weiteren Gegenstand der Erfindung in an sich bekannter Weise dadurch hergestellt werden, daß man Polyisobutylenbernsteinsäureanhydrid mit äquimolaren Mengen des Alkohols R20H oder R30H unter an sich bekannten Veresterungsbedingungen und vorzugsweise in Gegenwart eines Lösungsmittels umsetzt.According to another aspect of the invention, the compounds according to the invention can be prepared in a manner known per se by reacting polyisobutylene succinic anhydride with equimolar amounts of the alcohol R 2 0H or R 3 0H under esterification conditions known per se and preferably in the presence of a solvent.
Unter an sich bekannten Veresterungsbedingungen sind dabei die dem Fachmann bekannten Bedingungen zu verstehen, unter denen üblicherweise Veresterungen durchgeführt werden. Hierzu gehört die Anwendung erhöhter Temperatur, vorzugsweise einer Temperatur von 40 bis 100 °C. Man kann die Veresterungsreaktion vorteilhaft unter Verwendung eines Lösungsmittels durchführen. Die Veresterungsreaktion kann in Gegenwart an sich bekannter Katalysatoren, wie z. B. geringer Mengen tertiärer Amine, durchgeführt werden. Um eine unerwünschte Polymerisation der Acrylat- bzw. Methacrylatgruppen zu vermeiden, kann man geringe Mengen, z. B. 0,02 bis 1 Gew.-%. Polymerisationsinhibitoren, wie Hydrochinon, zufügen.Esterification conditions known per se are understood to mean the conditions known to the person skilled in the art under which esterifications are usually carried out. This includes the use of elevated temperatures, preferably a temperature of 40 to 100 ° C. The esterification reaction can advantageously be carried out using a solvent. The esterification reaction can in the presence of known catalysts, such as. B. small amounts tertiary amines. In order to avoid undesired polymerization of the acrylate or methacrylate groups, small amounts, e.g. B. 0.02 to 1 wt .-%. Add polymerization inhibitors such as hydroquinone.
Ein weiterer Gegenstand der Erfindung sind Zubereitungen, die durch Bestrahlung Klebmittel bilden, bestehend aus 30 bis 100 Gew.-% Verbindungen des Patentanspruchs 1,0 bis 70 Gew.-% durch Strahlung polymerisierbare Monomere und/oder Oligomere, 0 bis 15 Gew.-% Initiatoren und 0 bis 50 Gew.-% üblicher Zusatzmittel, wie Klebhilfsmittel, Pigmente und Füllstoffe.The invention further relates to preparations which form adhesives by radiation, consisting of 30 to 100% by weight of compounds of patent claim 1.0 to 70% by weight of radiation-polymerizable monomers and / or oligomers, 0 to 15% by weight. % Initiators and 0 to 50% by weight of conventional additives, such as adhesive aids, pigments and fillers.
Die erfindungsgemäßen Zubereitungen enthalten mindestens 30 Gew.-% der Verbindungen des Patentanspruchs 1. Sie können bis zu 70 Gew.-% durch Strahlung polymerisierbare Monomere und/oder Oligomere enthalten. Beispiele solcher Monomeren oder Oligomeren sind Hexandioldiacrylat, 2-Ethylhexylacrylat, Trimethylolpropantriacrylat oder sogenannte Epoxyacrylate, die beispielsweise von Bisphenol A abgeleitet sind, Urethanacrylate und Polyesteracrylate, Eigenschaften der Klebmittel, insbesondere die Viskosität und/oder die Härtungsgeschwindigkeit und/oder die Klebeigenschaften, zu beeinflussen.The preparations according to the invention contain at least 30% by weight of the compounds of claim 1. They can contain up to 70% by weight of radiation-polymerizable monomers and / or oligomers. Examples of such monomers or oligomers are hexanediol diacrylate, 2-ethylhexyl acrylate, trimethylolpropane triacrylate or so-called epoxy acrylates, which are derived, for example, from bisphenol A, urethane acrylates and polyester acrylates, properties of the adhesives, in particular the viscosity and / or the curing rate and / or the adhesive properties.
Die erfindungsgemäßen Zubereitungen können bis zu 15 Gew.-% Initiatoren enthalten. Bei der Polymerisation der in den erfindungsgemäßen Zubereitungen enthaltenen Verbindungen des Anspruchs 1 durch Elektronenstrahlen kann man auf den Zusatz von Initiatoren verzichten. Sie werden jedoch bei der Aushärtung durch UV-Strahlen benötigt. Geeignete Initiatoren sind aromatische Ketone, Hydroxyketone, Benzoinether und andere hierfür bekannte Verbindungen, die gegebenenfalls auch aktivierende Zusätze, wie Amine, enthalten können.The preparations according to the invention can contain up to 15% by weight of initiators. In the polymerization of the compounds of claim 1 contained in the preparations according to the invention by electron beams, the addition of initiators can be dispensed with. However, they are required for curing by UV rays. Suitable initiators are aromatic ketones, hydroxyketones, benzoin ethers and other compounds known for this purpose, which may also contain activating additives such as amines.
Die erfindungsgemäßen Zubereitungen können bis zu 50 Gew.-% übliche Zusatzstoffe enthalten. Übliche Zusatzstoffe sind z. B. Mittel, welche zur Beeinflussung der Klebeigenschaften zugemischt werden und als Klebhiffsmittel bezeichnet werden. So ist es beispielsweise möglich, Polyisobutylen, welches frei von funktionellen Gruppen ist, zuzumischen. Es ist ferner möglich, Pigmente und/oder Füllstoffe zuzusetzen soweit sie nicht die Haftklebereigenschaften beeinträchtigen. Die Verwendung von Lösungsmitteln ist möglich, aber wird im allgemeinen vermieden, da es gerade ein Vorteil der erfindungsgemäßen Verbindungen ist, daß sie aufgrund ihrer Konsistenz lösungsmittelfrei verarbeitet werden können.The preparations according to the invention can contain up to 50% by weight of conventional additives. Common additives are e.g. B. agents which are admixed to influence the adhesive properties and are referred to as adhesive agents. For example, it is possible to mix in polyisobutylene which is free of functional groups. It is also possible to add pigments and / or fillers as long as they do not impair the adhesive properties. The use of solvents is possible, but is generally avoided, since it is an advantage of the compounds according to the invention that, because of their consistency, they can be processed without solvents.
Typische Beispiele für erfindungsgemäße Klebhilfsmittel sind klebrig machende Produkte, wie z. B. Polybutylene, Polybutadiene, Polyisoprene, Polychloroprene, Polyacrylate, Polyvinylacetate verschiedener Molekulargewichte, Naturkautschuk, Naturharzester, sogenannte Kohlenwasserstoffharze. Weitere geeignete Produkte sind dem Fachmann z. B. aus der DE-OS 2 340 040 bekannt.Typical examples of adhesive aids according to the invention are tackifying products, such as. B. polybutylenes, polybutadienes, polyisoprenes, polychloroprenes, polyacrylates, polyvinyl acetates of various molecular weights, natural rubber, natural resin esters, so-called hydrocarbon resins. Other suitable products are the expert z. B. from DE-OS 2 340 040 known.
Geeignete Füllstoffe sind Calciumcarbonat, Kieselsäure, Ruß, Talkum und Silicate.Suitable fillers are calcium carbonate, silica, carbon black, talc and silicates.
52,8 g (0,05 m) eines Polyisobutylenbernsteinsäureanhydrids vom Molekulargewicht 1056 und 14,9 g Pentaerythrittriacrylat wurden als 50%ige Lösung in Toluol 60 h bei Raumtemperatur gerührt. Nach Entfernen des Lösungsmittels wurde sodann eine braune Flüssigkeit mit einer Viskosität von 45 000 mPa . s erhalten.
- Säurewert : 0,70 · 10-3 mg KOH/g Substanz (theoretisch 0,71 . 10-3).
- Typische IR-Banden :
- 1366 cm-1 m} Polyisobutylen-Teil des Moleküls
- 1390 cm-1 m}
- 810 cm-1 m}
- 1410 cm-1 s Acrylat-Teil des Moleküls
- 1735 cm-1 s
- m = mittel
- s = stark
- Acid value: 0.70 x 10 -3 mg KOH / g substance (theoretically 0.71. 10 -3 ).
- Typical IR bands:
- 1366 cm -1 m} polyisobutylene part of the molecule
- 1390 cm -1 m}
- 810 cm -1 m}
- 1410 cm -1 s acrylate part of the molecule
- 1735 cm -1 s
- m = medium
- s = strong
52,8 g des Polyisobutylenbemsteinsäureanhydrids aus Beispiel 1 wurden mit 5,8 g 2-Hydroxyethylacrylat als 50 %ige Lösung in Toluol 3 h bei 60 °C gerührt und dann im Vakuum vom Lösungsmittel befreit. Man erhält eine braune Flüssigkeit mit einer Viskosität von 23 000 mPa . s.
- Säurewert : 0,80 . 10-3 mg KOH/g Substanz (theoretisch 0,82 . 10-3).
- Typische IR-Banden :
- 1366 cm-1 m } Polyisobutylen-Teil des Moleküls
- 1390 cm-1 m
- 810 cm-1 w }
- 1410 cm-1 w Acrylat-Teil des Moleküls
- 1735 cm-1 s
- m = mittel
- s =stark
- w = schwach
- Acid value: 0.80. 10 -3 mg KOH / g substance (theoretically 0.82. 10 -3 ).
- Typical IR bands:
- 1366 cm -1 m} polyisobutylene part of the molecule
- 1390 cm -1 m
- 810 cm -1 w}
- 1410 cm -1 w acrylate part of the molecule
- 17 35 cm- 1 s
- m = medium
- s = strong
- w = weak
146 g (0,05 m) eines Polyisobutylenbernsteinsäureanhydrids vom Molekulargewicht 2920 und 6,5 g 2-Hydroxypropylacrylat wurden als 50 %ige Lösung in Toluol 5 h bei 85 °C gerührt. Nach Entfernen des Lösungsmittels wurde eine braune Flüssigkeit mit einer Viskosität von 39 000 mPa - s erhalten.146 g (0.05 m) of a polyisobutylene succinic anhydride of molecular weight 2920 and 6.5 g of 2-hydroxypropyl acrylate were stirred as a 50% solution in toluene at 85 ° C. for 5 hours. After removal of the solvent, a brown liquid with a viscosity of 39,000 mPas was obtained.
Säurewert : 0,31 . 10-3 mg KOH/g Substanz (theoretisch 0,33 . 10-3).Acid value: 0.31. 10 -3 mg KOH / g substance (theoretically 0.33.10 -3 ).
Typische IR-Banden wie in Beispiel 2.Typical IR bands as in Example 2.
Die Produkte der Beispiele 1 bis 3 sowie die in der folgenden Tabelle aufgeführten Zubereitungen aus diesen Produkten wurden mit 8 % Diethoxyacetophenon vermischt und durch Belichtung mit einer UV-Mitteldruck-Hg-Lampe (80 W/cm) während 1 bis 3 Sek. in einer Schichtdicke von 20 µm auf einem 90 g/m 2 Papier gehärtet.
Von den beschichteten und UV-bestrahlten Papieren wurden 3 cm breite Streifen durch fünfmaliges Walzen mit einer 9 kg schweren Walze auf Polybutylenterephthalat sowie auf chromsäurevorbehandeltes Aluminium aufgebracht. Bei dem Versuch, die Papierstreifen, die mit den zu klebrigen Produkten ausgehärteten Zubereitungen 1 bis 9 beschichtet worden waren, von den Substraten Polyester und Aluminium zu lösen, wurde in allen Fällen das Papier zerstört.3 cm wide strips of the coated and UV-irradiated papers were applied by rolling five times with a 9 kg roller on polybutylene terephthalate and on chromium acid-pretreated aluminum. In all cases, the paper was destroyed in an attempt to detach the paper strips which had been coated with preparations 1 to 9 which had cured to form sticky products from the substrates polyester and aluminum.
Ohne UV-Härtung dringen dagegen die Zubereitungen 1 bis 9 in beschichtete Papiere ein. Diese Papiere lassen sich dann leicht von Polyester und Aluminium lösen, ohne zerstört zu werden.In contrast, without UV curing, preparations 1 to 9 penetrate coated papers. These papers can then be easily detached from polyester and aluminum without being destroyed.
Damit ist gezeigt, daß die erfindungsgemäß hergestellten Produkte und Zubereitungen aus dem flüssigen Zustand durch strahleninduzierte Polymerisation in feste Form überführt werden können. In dieser Form sind sie für die Anwendung als Haftkleber geeignet.This shows that the products and preparations produced according to the invention can be converted from the liquid state into solid form by radiation-induced polymerization. In this form, they are suitable for use as pressure sensitive adhesives.
Claims (3)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3323913A DE3323913C2 (en) | 1983-07-02 | 1983-07-02 | Polyisobutylene succinic acid half esters, their production and their use for the production of an adhesive |
| DE3323913 | 1983-07-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| EP0130459A2 EP0130459A2 (en) | 1985-01-09 |
| EP0130459A3 EP0130459A3 (en) | 1985-05-29 |
| EP0130459B1 true EP0130459B1 (en) | 1986-09-10 |
Family
ID=6203005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP84106997A Expired EP0130459B1 (en) | 1983-07-02 | 1984-06-19 | Polyisobutylene succinic acid half esters, their preparation and compositions containing these compounds that can be transferred to an adhesive by means of radiation |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US4533723A (en) |
| EP (1) | EP0130459B1 (en) |
| DE (1) | DE3323913C2 (en) |
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| US6989407B2 (en) * | 2004-01-09 | 2006-01-24 | Northwest Coatings, Llc | Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers |
| EP2084219B1 (en) * | 2006-10-24 | 2012-09-05 | Lubrizol Limited | Polymeric coupling agents |
| US8597784B2 (en) | 2010-09-30 | 2013-12-03 | 3M Innovative Properties Company | Radiation curable poly(isobutylene) adhesive copolymers |
| US20120122359A1 (en) * | 2010-11-16 | 2012-05-17 | 3M Innovative Properties Company | Ionically crosslinkable poly(isobutylene) adhesive polymers |
| JP2014500354A (en) | 2010-11-16 | 2014-01-09 | スリーエム イノベイティブ プロパティズ カンパニー | UV curable anhydride modified poly (isobutylene) |
| US8663407B2 (en) | 2010-11-17 | 2014-03-04 | 3M Innovative Properties Company | Isobutylene (Co)polymeric adhesive composition |
| US8629209B2 (en) | 2010-12-02 | 2014-01-14 | 3M Innovative Properties Company | Moisture curable isobutylene adhesive copolymers |
| US8962767B2 (en) | 2011-02-15 | 2015-02-24 | 3M Innovative Properties Company | Isobutylene copolymer with grafted polymer groups |
| KR101929088B1 (en) * | 2012-04-27 | 2018-12-13 | 헨켈 아이피 앤드 홀딩 게엠베하 | Grafted telechelic polyisobutylenes possessing reactive functionality, processes for preparing the same and curable compositions comprising the same |
| EP2885363B1 (en) | 2012-08-14 | 2018-02-07 | 3M Innovative Properties Company | Adhesives comprising grafted isobutylene copolymer |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4946886B1 (en) * | 1970-10-19 | 1974-12-12 | ||
| US4148605A (en) * | 1976-10-07 | 1979-04-10 | Mobil Oil Corporation | Rust inhibitor and compositions thereof |
| GB1543359A (en) * | 1976-10-28 | 1979-04-04 | Shell Int Research | Esterification of hydrocarbyl-substituted succinic anhydrides |
| US4124571A (en) * | 1977-08-01 | 1978-11-07 | National Starch And Chemical Corporation | Thermoplastic copolyesters prepared from aromatic dicarboxylic acid substituted succinic acid or anhydride and a glycol and the use thereof in adhesives |
| JPS5516002A (en) * | 1978-06-23 | 1980-02-04 | Hitachi Chem Co Ltd | Resin composition for forming |
| US4151057A (en) * | 1978-08-14 | 1979-04-24 | Shell Oil Company | High temperature adhesive made by exposure to radiation |
| US4255589A (en) * | 1979-06-29 | 1981-03-10 | Exxon Research & Engineering Co. | Process for the production of oil-soluble polyol esters of dicarboxylic acid materials in the presence of a metal salt of a hydroxy aromatic compound |
| US4375540A (en) * | 1981-08-31 | 1983-03-01 | Eastman Kodak Company | Polyester modified with alkyl- or alkenylsuccinic anhydrides |
-
1983
- 1983-07-02 DE DE3323913A patent/DE3323913C2/en not_active Expired
-
1984
- 1984-06-19 EP EP84106997A patent/EP0130459B1/en not_active Expired
- 1984-06-28 US US06/625,712 patent/US4533723A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE3323913C2 (en) | 1986-01-02 |
| EP0130459A2 (en) | 1985-01-09 |
| US4533723A (en) | 1985-08-06 |
| EP0130459A3 (en) | 1985-05-29 |
| DE3323913A1 (en) | 1985-01-10 |
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